Record Information
Version1.0
Creation date2018-05-02 12:32:02 UTC
Update date2018-05-04 14:22:51 UTC
FoodComEx IDPC001197
FoodDB RecordFDB001819
Chemical Information
NameHippuric acid
DescriptionHippuric acid (Gr. hippos, horse, ouron, urine) is a carboxylic acid found in the urine of horses and other herbivores. Hippuric acid crystallizes in rhombic prisms which are readily soluble in hot water, melt at 187 °C and decompose at about 240 °C. High concentrations of hippuric acid can also indicate a toluene intoxication. When many aromatic compounds such as benzoic acid and toluene are taken internally, they are converted to hippuric acid by reaction with the amino acid, glycine.; Hippuric acid is an acyl glycine formed by the conjugation of benzoic aicd with glycine. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction: acyl-CoA + glycine < -- > CoA + N-acylglycine. Hippuric acid is a normal component of urine and is typically increased with increased consumption of phenolic compounds (tea, wine, fruit juices). These phenols are converted to benzoic acid which is then converted to hippuric acid and excreted in the urine. Hippuric acid is the most frequently used biomarker in the biological monitoring of occupational exposure to toluene. This product of solvent biotransformation may be also found in the urine of individuals who have not been exposed to the solvent. A smaller fraction of the absorbed toluene is oxidized to aromatic compounds including ortho-cresol, which is not found significantly in the urine of nonexposed individuals. The concentration of hippuric acid in the urine of individuals exposed to a low toluene concentration does not differ from that of individuals not exposed to the solvent. This has led to the conclusion that hippuric acid should not be utilized in the biological monitoring of occupational exposure to low levels of toluene in the air.; Protein-bound organic acids such as hippuric acid are markedly accumulated in uremic plasma and produce defective protein binding of drugs. (PMID: 9120876, 8734460).
CAS Number495-69-2
Structure
Thumb
Synonyms
SynonymSource
(benzoylamino)-acetatebiospider
(benzoylamino)-acetic acidbiospider
(benzoylamino)acetic acidbiospider
2-benzamido-acetic acidbiospider
2-Benzamidoacetatebiospider
2-Benzamidoacetic acidbiospider
532-93-4 (mono-ammonium salt)biospider
532-94-5 (mono-hydrochloride salt)biospider
583-10-8 (mono-potassium salt)biospider
Acetic acid, (benzoylamino)-biospider
Acetic acid,benzamide hippuric acidbiospider
Acido ippuricobiospider
Benzamidoacetatebiospider
Benzamidoacetic acidbiospider
Benzaminoacetic acidbiospider
Benzenecarboxamide, n-carboxymethyl-biospider
Benzoylaminoacetic acidbiospider
Benzoylglycinbiospider
Benzoylglycinebiospider
Benzoylglycocollbiospider
Glycine, n-benzoyl-biospider
Hippuratebiospider
Hippuricum acidumbiospider
N-(phenylcarbonyl)glycinebiospider
N-benzoyl-glycinbiospider
N-benzoylglycinebiospider
Phenylcarbonylaminoacetatebiospider
Phenylcarbonylaminoacetic acidbiospider
Chemical FormulaC9H9NO3
IUPAC name2-(phenylformamido)acetic acid
InChI IdentifierInChI=1S/C9H9NO3/c11-8(12)6-10-9(13)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)(H,11,12)
InChI KeyQIAFMBKCNZACKA-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CNC(=O)C1=CC=CC=C1
Average Molecular Weight179.1727
Monoisotopic Molecular Weight179.058243159
Chemical Taxonomy
Description belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHippuric acids
Alternative Parents
Substituents
  • Hippuric acid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Benzoyl
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logP0.31HANSCH,C ET AL. (1995)
Experimental Water Solubility3.75 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point187-191 oC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity Available1 to 2 mg
Delivery Time2 weeks
Storage Formpowder
Storage ConditionsRT
StabilityNot Available
Purityunknown
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Augustin ScalbertInternational Agency for Research on Cancer (IARC), Biomarkers Group, 150 cours Albert Thomas, Lyon, FR, 69372scalberta@iarc.fr
Commercial Vendors
AKSci F131
AKSci J93268
Glentham GM5145
MetaSci HMDB0000714
Sigma-Aldrich HMDB0000714
Toronto Research Chemicals H356700